Direct Amino-α-C-H Heteroarylation of Amides under Electrochemical Conditions

Org Lett. 2024 Jan 19;26(2):493-497. doi: 10.1021/acs.orglett.3c03868. Epub 2024 Jan 8.

Abstract

An electrochemical hydrogen atom transfer (HAT) strategy for the direct amino-α-C-H heteroarylation of amides is described. The cheap TMSN3 acts as a hydrogen atom transfer reagent. A series of heteroarenes including quinoxalin-2(1H)-ones, 4-methylquinoline, isoquinoline, 2-methylquinoxaline, benzothiazole, etc., and various readily available amides/lactams were suitable. The reaction has the characteristics of a wide range of substrates, good regioselectivity, chemical oxidant-free conditions, etc.